Nonsymmetrical bipiperidyls as inhibitors of vesicular acetylcholine storage

SMN Efange, A Khare, SM Parsons, R Bau…

Index: Efange; Khare; Parsons; Bau; Metzenthin Journal of Medicinal Chemistry, 1993 , vol. 36, # 8 p. 985 - 989

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Citation Number: 29

Abstract

Introduction of a nitrogen atom into the cyclohexane ring of 2-(4-phenylpiperidinyl) cyclohexanol (vesamicol, AH5183) yielded two positional isomers, 5-azavesamicol (5, prezamicol) and 4-azavesamicol (6, trozamicol). As inhibitors of vesicular acetylcholine transport, 5 and 6 were found to be 147 and 85 times less potent than vesamicol. N- Benzoylation of 5 (to yield 9a) increased the potency 3-fold. In contrast, loa, a compound ...